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Holiday rentals in Kailua

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Top-rated holiday rentals in Kailua

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A covered patio area is viewed, featuring a large umbrella providing shade over a small table. The entrance to the unit is visible in the background, framed by a railing and surrounded by greenery.
Home in Kailua
4.87 out of 5 average rating, 473 reviews

Kailua Beach Park - 1 BR Cottage

Kailua Beach was once again been rated as the best beach in the USA for 2019, by Dr. Beach." The cottage is directly across the street from Kailua Beach Park and less than a 2-minute walk to step into the ocean. It is a legal vacation rental, license number 1990/NUC-1758. The property is tucked away one house back from the road into Lanikai, and described by guests as "a little oasis of quiet and calm." The bathroom has been remodeled with a new showers, sinks and plumbing fixtures April 2022!

Superhost
Home in North Shore
4.76 out of 5 average rating, 116 reviews

North shore Studio with sauna! - Walk to beach!

Legal Nightly Vacation Rental (No 30-day contracts) A cozy, island-style unit with a loft bed, perfect for an authentic Hawaiian getaway. The unit includes High speed WiFi, 65 inch Smart TV, Split unit AC, sauna, an outdoor shower, an outdoor gym, a sun deck, and private access. Located within walking distance to famous Waimea Bay and other beautiful spots, this space offers convenience, comfort, and island charm. **Please note bookings after may 15th the sauna will be removed for renovations!

Guest favourite
A spacious balcony is featured, offering a direct view of the ocean and beach. A lounge chair and a round table are positioned for relaxation. A woman is seated, enjoying the scenery. The space is filled with natural light from the large sliding glass doors.
Apartment in Waikiki
4.93 out of 5 average rating, 151 reviews

Beachfront Home (Car & Parking Available)

* Aloha! Welcome to our happy place - our beachfront home! * Featuring a direct ocean view from an entire wall of windows, where you can see the ocean, beach, lagoon, surfers, whales, sunsets, and more. The location is right on Waikiki Beach. You are within minutes of walking distance to almost everything - beaches, restaurants, bars, surfing lessons, boat tours, grocery stores, shopping malls and more. Every time I come to Hawaii, I am happy. I hope our place can bring you happiness too. :-)

Guest favourite
A spacious studio suite features a king-size bed centered against a vibrant tropical-themed wall art. A dining area with a glass table and wicker chairs sits adjacent, while a cozy seating area with floral-patterned cushions completes the inviting layout. Ample natural light filters through the windows.
Guest suite in Kailua
4.92 out of 5 average rating, 368 reviews

Kailua Pineapple Studio. Walk to Beach! PERMITTED

Legal, permitted short-term rental (Permit #1990/NUC-1819, Tax map key:43073024) *not impacted by Honolulu ordinances banning Short-term Rentals Hawaiian style, modern appointments. Beautiful 450 sf suite in the one of the most desirable locations in Hawaii, Kailua! An easy 8-10 min. walk to Kailua Beach, top rated in the world. Private residence at the end of a quiet cul-de-sac. Airbnb “Guest Favorite” awardee! Sister Unit: Kailua Palm Studio. Walk to Beach! PERMITTED Managed by Kupono Svcs.

Top guest favourite
A modern two-story home is situated within a well-maintained community. The exterior features light gray siding with white trim and a spacious driveway leading to a two-car garage. Lush greenery is visible in the landscaped yard, with the majestic mountains serving as a backdrop.
Home in Makaha Valley
4.99 out of 5 average rating, 109 reviews

4BR, Near Beach, Pool/Spa, Gym, Free Parking, BBQ

Discover your dream vacation, just 2 miles from the world-famous Makaha Beach. This pristine rental is perfect for those seeking an authentic Hawaiian experience! ~Stunning Views: From every room including the backyard! ~Culinary Delights: Create island feasts in our fully equipped kitchen. ~Cozy Comfort: Rest easy in plush bedrooms designed for ultimate relaxation. ~Adventure Awaits: Surfing, fishing, & more are within easy reach. Don't miss out on making memories that will last a lifetime!

Guest favourite
A tranquil outdoor area features a 60-foot lap pool surrounded by lush greenery and natural rock elements. A wooden dining table with an umbrella is positioned nearby, offering a view of the ocean in the background and a waterfall cascading into the pool.
Guest house in Kailua
4.8 out of 5 average rating, 198 reviews

Absolutely Oceanfront-60'Waterfall Pool-Legal

Kailua Absolutely Oceanfront Deluxe Vacation Rental The closest house to the Ocean in Kailua Hear waves breaking just outside Located in a quiet uncongested upscale neighborhood 60ft salt-sanitized waterfall lap pool Attached Ocean-View Deck 16-foot vaulted ceilings Wall-mounted Fujitsu air conditioning Tide pooling steps away Dramatic Sunrises Refreshing Tradewinds No Bedbugs here/Bed Bug Protective Queen Mattress and pillow covers Ozone sanitized between rentals NUC: Certificate 90-BB-0060

Top guest favourite
A scenic sunset view highlights the horizon over calm waters, with soft waves lapping against the sandy beach. In the foreground, a decorative dolphin sculpture adds a touch of charm to the balcony railing, while lush greenery frames the view.
Apartment in Waianae
4.97 out of 5 average rating, 321 reviews

Beachfront Getaway - Hawaiian Princess Condo

Mesmerizing sunset views from this sandy beach front condo. Nothing separates you from sparkling turquoise waters but footprints in the sand. Balcony is ideal height for turtle watching. From Nov- April you may spot a whale. This vibrant land is full of surprises. Even dolphins spin by now and then. Escape the crowds of Waikiki to experience a real Hawaiian lifestyle. Snorkel, boogie board or surf right out your door. Awakening to the rhythm of the ocean can change your life forever.

Guest favourite
A tropical pathway leads from a sandy beach to the bright blue ocean, with gentle waves lapping against the shore. Lush greenery borders the scene, while distant hills are visible on the horizon under a partly cloudy sky.
Place to stay in Kailua
4.96 out of 5 average rating, 109 reviews

Nai’a Suite at La Bella’s-Walk to Beach-Licensed

La Bella’s B&B is a High End Luxury home filled with charm and a touch of farmhouse/beach elegance. Two Suites are available for booking. Owners live onsite. Starbucks, Safeway, Gas Stations and Eateries are right across the street. Nai’a (Dolphin) Suite Offers: -Kitchenette -Private Bathroom -Separate Entrance -AC and Powerful high end fan -King size bed w/luxury bedding If you want a beautiful garden, great host family and a short walk to the beach this is the place for you.

Top guest favourite
A modern dining area features a large wooden table surrounded by eight upholstered chairs. Natural light fills the space through expansive sliding glass doors, which provide scenic ocean views. A decorative plant adds a touch of greenery, while an artwork piece complements the contemporary decor.
Apartment in Waikiki
4.97 out of 5 average rating, 190 reviews

Penthouse, 2-Minute Walk to Beach/Free Parking

1700+ SQ. FT., FREE GARAGE PARKING AND WIFI. TWO-MINUTE WALK TO THE BEACH. Located in the hotel zone and in compliance with short-term rental laws, this gorgeous, remodeled Penthouse with Diamond Head and Ocean Views, located just 1.5 blocks from Waikiki Beach and the Honolulu Zoo, this 1,700+ s.f. (153.93 square meters) condo offers the style and comfort of a luxury hotel with a huge luxurious lanai, a large chef's kitchen, and a full-size washer and dryer.

Guest favourite
An open dining area is highlighted by a large wooden table with seating for six, complemented by natural light from sliding glass doors. The adjacent kitchen features modern appliances and a spacious island with bar seating, creating a welcoming atmosphere for gatherings.
Home in Waianae
4.97 out of 5 average rating, 119 reviews

Hawaiian Pakele (escape)

Aloha and welcome to our home!! Newly built and luxuriously appointed, this beautiful 3 bedroom and 2.5 bathroom house is the ideal spot on the west side of Oahu. Located in the private gated community, with breath taking views of ocean and mountains and only a 3-min drive to the world famous Makaha beach. This is the most desirable location for families, friends and couples to escape, relax and enjoy a rejuvenating and memorable vacation!

Superhost
A spacious living area features large windows offering panoramic ocean views. Modern furnishings include a soft sofa adorned with decorative pillows, a stylish armchair, and a wooden dining table. Natural light brightens the room, enhancing the fresh coastal ambiance.
Apartment in Waikiki
4.91 out of 5 average rating, 132 reviews

32nd Floor Penthouse. 3min walk to Waikiki Beach

Welcome to HaleHinano Penthouse – Waikiki Beach. This rarely available 1-bedroom penthouse on the 32nd floor offers panoramic ocean views and modern renovated interiors. Located just a 3-minute walk to the center of Waikiki Beach, the location is everything—and so are the views! The unit includes an in-unit washer and dryer, and guests can enjoy the rooftop pool, jacuzzi, and BBQ area. On-site parking is available for $35 per day.

Superhost
A serene beach scene features soft white sand leading to clear turquoise waters. Gentle waves lap against the shoreline under a bright blue sky with scattered clouds. Lush greenery borders the beach, providing a natural frame to the picturesque landscape.
Guest house in Kailua
4.78 out of 5 average rating, 170 reviews

Kailua Beach Cottage - 1990/NUC-1797

WE HAVE PERMIT - 90/TVU-0287 FROM THE CITY & COUNTY WE WERE RATED BY AIRBNB AS A SUPERHOST. KAILUA BEACH RATED #1 BEACH IN AMERICA! This place is good for couples, business travelers, and families. (On the 2nd floor - upstairs) *Additional guest fee of $90 per person per day applies to parties over 4 people. Additional service fee and tax will apply. Visit the 8 Bdrm Villa website for a larger family group.

Popular amenities for Kailua holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Kailua's top sights

Lanikai Beach

465 locals recommend

Kailua Beach Park

217 locals recommend

Lanikai Pillbox Hike

263 locals recommend

Other great holiday rentals in Kailua

Top guest favourite
Apartment in Waikiki
4.97 out of 5 average rating, 29 reviews

NEW! Aloha OceanView Haven @IlikaiResort w/Parking

Superhost
A cozy sleeping area is visible with a spacious bed topped with crisp white linens and a textured green pillow. A bedside table holds a blue and white lamp and a digital clock. Light enters through a nearby window, softly illuminating the space.
Tiny home in North Shore
4.91 out of 5 average rating, 45 reviews

North Shore Farm Cottage

Top guest favourite
A spacious bedroom features wooden beam ceilings and is adorned with a coral-patterned bedspread draped over a king-size bed. A small desk is positioned near the window, and natural light filters through sheer curtains. A large area rug with a nautical design enhances the coastal theme.
Guest house in Kailua
4.97 out of 5 average rating, 29 reviews

Private 1 Bedroom Cottage

Apartment in Ko Olina
4.85 out of 5 average rating, 26 reviews

Hale Lanikai | Ko Olina | Penthouse Ko Olina Villa

Guest favourite
The image captures a sunset view over the ocean, framed by palm trees and a neighboring cottage's overhang. A grassy area leads to the water’s edge, where calm waves meet the shore. Light reflects off the water, creating a serene ambiance.
Cottage in North Shore
4.87 out of 5 average rating, 149 reviews

Best Kept Secret on Oahu! and WE ARE LICENSED!!!

A serene beach scene features soft golden sand and clear turquoise waters, bordered by lush greenery and palm trees. Sunbathers can be seen along the shore, while gentle waves lap against a reef structure in the distance, creating a peaceful coastal atmosphere.
Flat in Kahuku
4.78 out of 5 average rating, 32 reviews

Iconic Turtle Bay - Full Kitchen & 2 Full Baths

Flat in Kahuku
5 out of 5 average rating, 3 reviews

North Shore Hideaway

Superhost
A balcony features two comfortable chairs and a small table, offering an unobstructed view of the ocean. The tranquil waters display shades of blue and green, while a hanging lantern provides subtle illumination.
Apartment in Waianae
4.84 out of 5 average rating, 108 reviews

Ocean Front Retreat. Private Beach. Pool. HotTub

When is the best time to visit Kailua?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$320 SGD$321 SGD$289 SGD$289 SGD$304 SGD$304 SGD$304 SGD$295 SGD$275 SGD$261 SGD$282 SGD$277 SGD
Avg. temp22°C22°C23°C24°C24°C26°C26°C27°C26°C26°C24°C23°C

Frequently Asked Questions

  • What are the best places to stay in Kailua?

    Stays in central Kailua let you explore vibrant shops and restaurants, while accommodations near Lanikai offer relaxed beach access. Both areas are frequently suggested for those looking for a local experience.

  • What are the best things to do in Kailua with kids?

    Kailua Beach Park has gentle waves for swimming, and the Kalapawai Market is known for casual snacks and treats. Kayaking on the bay and exploring nearby nature trails are also frequently suggested for families.

  • What are some of the best things to do in Kailua?

    Explore kayaking or paddleboarding in the calm bay, hike up to the Lanikai Pillboxes, and unwind at Kailua Beach Park. Kailua’s farmers' markets, local eateries, and bike paths are also frequently suggested.

  • How is the weather in Kailua?

    Kailua has warm temperatures throughout the year, ranging from about 65–85°F (18–30°C). Rain is more frequent in winter and early spring, while summers are sunnier with less rainfall.

  • When is the best time to visit Kailua?

    May through September has warmer temperatures around 70–85°F (21–30°C) and less rainfall, making it a popular time for beach outings. Late spring and early fall are often enjoyed for smaller crowds and local festivals.

  • What are the best places to visit in Kailua?

    Frequently suggested spots in Kailua include the white sands of Kailua Beach Park, the scenic Lanikai Beach, and the Pillbox Hike for panoramic coastal views. The neighborhood also has inviting local markets and art galleries.

  • What are some hiking trails in Kailua?

    The Lanikai Pillbox Hike is frequently suggested for its scenic coastal views and moderate climb. Locals also explore forested paths in nearby natural reserves, where you can experience native plants and ocean breezes.

  • What are some family activities we can do in Kailua?

    Families can explore calm swimming beaches, rent bikes for easy paths, or visit local playgrounds in Kailua. Kayaking, visiting markets, or observing wildlife at Kawainui Marsh are also popular choices among visitors with children.

  • What are some of the best day trip ideas from Kailua?

    Day trips around Kailua can include exploring lush botanical gardens, visiting the North Shore’s surf spots, or hiking in forested preserves. The area also has popular historic sites and cultural centers within easy reach.

  • Are there any pet friendly accommodations available in Kailua?

    Many accommodations in Kailua are pet friendly, especially around central neighborhoods and residential areas. Parks and outdoor cafes make it convenient for guests traveling with pets.

  • What are some local tips for visiting Kailua?

    Weekdays generally feel quieter at popular beaches, and early mornings are good for catching sunrise views from Lanikai. Remember to respect local customs, pack out what you bring, and use reef-safe sunscreen to protect marine life.

  • What is Kailua known for?

    Kailua is known for its wide, sandy beaches, calm turquoise waters, and relaxed community vibe. The area has scenic hiking, local food spots, and opportunities to experience traditional Hawaiian culture.

  • What are the best hidden gems to explore in Kailua?

    Kailua has quiet local beaches, shaded marsh trails for birdwatching, and small independent shops where you can explore local crafts. Consider wandering untouristed sections of Kailua Beach or the nearby Kawainui Marsh trail for a more laid-back experience.

  • What are the best foods to try in Kailua?

    Kailua has fresh poke bowls, local plate lunches, and tropical fruit smoothies that are often recommended. Shave ice and pastries from neighborhood bakeries add to the area’s favorite flavors.

  • What should I bring for a trip to Kailua?

    Pack light, breathable clothing, swimwear, reef-safe sunscreen, and a sun hat for comfort in Kailua's warm weather. If you plan to hike or explore nature, closed-toe shoes and a reusable water bottle are often recommended.

  • What is the nightlife in Kailua like?

    Kailua has a relaxed nightlife scene with welcoming bars, laid-back dining spots, and venues that occasionally feature live music. Most nightlife is concentrated in town, and evenings often center around enjoying local flavors in a casual atmosphere.

  • What are the most popular events or festivals in Kailua?

    Kailua frequently hosts street fairs, annual parade celebrations around holidays, and open-air art markets. Late spring and holiday weekends are often filled with local music, food, and craft events.

  • Are there family friendly vacation rentals in Kailua?

    Kailua has many family-friendly rentals, often located near beaches or local parks. These options typically include amenities like kitchens, outdoor space, and easy access to nearby attractions.

Quick stats about holiday rentals in Kailua

  • Total holiday rentals

    Explore 340 holiday rentals in Kailua

  • Nightly prices starting at

    Kailua holiday rentals start at $51 SGD per night before taxes and fees

  • Verified guest reviews

    Over 11,150 verified reviews to help you choose

  • Family-friendly holiday rentals

    190 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    90 properties feature pools

  • Rentals with dedicated workspaces

    160 properties have a dedicated workspace

  • Wifi availability

    330 of Kailua holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Beachfront and Gym across Kailua rentals

  • 4.9 Average rating

    Kailua stays are highly rated by guests – averaging 4.9 out of 5!

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